Formal Dearomative Hydroamination of 2‑Arylphenols

An acid-promoted dearomative rearrangement of O-arylhydroxylamines affords 2-aminocyclohexadien-1-ones, which can in turn be reductively quenched for the synthesis of trans-aminoalcohols on a cyclohexadiene core. This method serves as an efficient entry to the pharmaceutically relevant 1-arylcyclohe...

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Bibliographic Details
Published in:Journal of organic chemistry 2025-01, Vol.90 (1), p.913-918
Main Authors: Wiley, Robert E., Eng, Michael C., Clarkson, Aidan J., Johnson, Jeffrey S.
Format: Article
Language:English
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Summary:An acid-promoted dearomative rearrangement of O-arylhydroxylamines affords 2-aminocyclohexadien-1-ones, which can in turn be reductively quenched for the synthesis of trans-aminoalcohols on a cyclohexadiene core. This method serves as an efficient entry to the pharmaceutically relevant 1-arylcyclohexylamine scaffold in two steps (one purification) from commercially available or readily prepared 2-arylphenols.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c02654